organic compounds
2-[5-(4-Fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thiazole
aApplied Organic Chemistry Department, National Research Centre, Dokki, 12622 Giza, Egypt, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: edward.tiekink@gmail.com
In the title compound, C25H20FN3S, two independent molecules comprise the which differ in the relative orientation of the fluorobenzene ring with respect to the pyrazole ring to which it is attached [dihedral angles = 89.39 (17) and 75.23 (16)° in the two molecules]. Each pyrazole ring adopts an with the methine C atom being the flap atom. There are additional twists in the molecules, e.g. between the five-membered rings [dihedral angles = 18.23 (16) and 17.84 (16)°] and between the thiazole and attached phenyl ring [10.26 (16) and 20.87 (15)°]. Overall, each molecule has a T-shape. In the crystal, molecules are connected into a three-dimensional architecture by weak C—H⋯π interactions.
Related literature
For the biological activity of pyrazolin-1-ylthiazoles, see: Abdel-Wahab et al. (2009, 2012); Chimenti et al. (2010). For a related structure, see: Fun et al. (2011).
Experimental
Crystal data
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Data collection: CrysAlis PRO (Agilent, 2011); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
10.1107/S1600536813004339/hg5292sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813004339/hg5292Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536813004339/hg5292Isup3.cml
A mixture of 5-(4-fluorophenyl)-3-p-tolyl-4,5-dihydro-1H-pyrazole-1-carbothioamide (0.31 g, 0.001 M) and 2-bromo-1-phenylethanone (0.2 g, 0.001 M) in anhydrous ethanol (30 ml) was heated under reflux for about 4 h. The resultant solid was filtered and dried. Re-crystallization was by slow evaporation of a DMF solution of (I) which yielded colourless crystals in 59% yield. M.pt. 418–420 K.
Carbon-bound H-atoms were placed in calculated positions (C—H = 0.93 to 0.98 Å) and were included in the
in the riding model approximation, with Uiso(H) = 1.2–1.5Uequiv(C).Data collection: CrysAlis PRO (Agilent, 2011); cell
CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 35% probability level. | |
Fig. 2. Overlay diagram of the two independent molecules in (I) with the S1-containing molecule illustrated in red. The molecules are overlaid so that the thiazolyl rings are superimposed. | |
Fig. 3. A view of the crystal packing in projection down the a axis. The C—H···π interactions are shown as purple dashed lines. |
C25H20FN3S | F(000) = 864 |
Mr = 413.50 | Dx = 1.303 Mg m−3 |
Monoclinic, Pc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P -2yc | Cell parameters from 5001 reflections |
a = 5.7563 (3) Å | θ = 2.9–27.5° |
b = 24.1214 (12) Å | µ = 0.18 mm−1 |
c = 15.1827 (8) Å | T = 295 K |
β = 90.948 (5)° | Prism, yellow |
V = 2107.83 (19) Å3 | 0.40 × 0.30 × 0.20 mm |
Z = 4 |
Agilent SuperNova Dual diffractometer with an Atlas detector | 9054 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 5841 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.042 |
Detector resolution: 10.4041 pixels mm-1 | θmax = 27.6°, θmin = 2.9° |
ω scan | h = −7→7 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | k = −31→31 |
Tmin = 0.837, Tmax = 1.000 | l = −19→19 |
22651 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.0492P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
9054 reflections | Δρmax = 0.14 e Å−3 |
543 parameters | Δρmin = −0.16 e Å−3 |
2 restraints | Absolute structure: Flack (1983), 4165 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.06 (6) |
C25H20FN3S | V = 2107.83 (19) Å3 |
Mr = 413.50 | Z = 4 |
Monoclinic, Pc | Mo Kα radiation |
a = 5.7563 (3) Å | µ = 0.18 mm−1 |
b = 24.1214 (12) Å | T = 295 K |
c = 15.1827 (8) Å | 0.40 × 0.30 × 0.20 mm |
β = 90.948 (5)° |
Agilent SuperNova Dual diffractometer with an Atlas detector | 9054 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | 5841 reflections with I > 2σ(I) |
Tmin = 0.837, Tmax = 1.000 | Rint = 0.042 |
22651 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.117 | Δρmax = 0.14 e Å−3 |
S = 0.99 | Δρmin = −0.16 e Å−3 |
9054 reflections | Absolute structure: Flack (1983), 4165 Friedel pairs |
543 parameters | Absolute structure parameter: −0.06 (6) |
2 restraints |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.49969 (14) | 0.29737 (3) | 0.50008 (6) | 0.0662 (2) | |
S2 | 1.01138 (13) | 0.25628 (3) | 0.36822 (6) | 0.0666 (2) | |
F1 | −0.0507 (5) | 0.34215 (9) | 0.99078 (17) | 0.1149 (8) | |
F2 | 0.5094 (5) | 0.12749 (9) | −0.12101 (16) | 0.1042 (7) | |
N1 | 0.1354 (4) | 0.32997 (10) | 0.58332 (16) | 0.0579 (6) | |
N2 | 0.2741 (4) | 0.24238 (11) | 0.62782 (17) | 0.0638 (7) | |
N3 | 0.4085 (4) | 0.19780 (11) | 0.60017 (17) | 0.0621 (7) | |
N4 | 0.8192 (4) | 0.17483 (10) | 0.28401 (16) | 0.0585 (6) | |
N5 | 0.6904 (4) | 0.26272 (10) | 0.23727 (18) | 0.0635 (7) | |
N6 | 0.6916 (4) | 0.31858 (10) | 0.26139 (16) | 0.0590 (7) | |
C1 | 0.0526 (5) | 0.42283 (12) | 0.52259 (19) | 0.0571 (8) | |
C2 | 0.1262 (6) | 0.46954 (15) | 0.4761 (2) | 0.0740 (9) | |
H2A | 0.2631 | 0.4680 | 0.4445 | 0.089* | |
C3 | −0.0020 (7) | 0.51781 (16) | 0.4767 (3) | 0.0822 (11) | |
H3 | 0.0519 | 0.5489 | 0.4470 | 0.099* | |
C4 | −0.2069 (7) | 0.52053 (16) | 0.5204 (3) | 0.0835 (11) | |
H4 | −0.2947 | 0.5529 | 0.5192 | 0.100* | |
C5 | −0.2824 (6) | 0.47491 (16) | 0.5663 (2) | 0.0758 (10) | |
H5 | −0.4214 | 0.4766 | 0.5965 | 0.091* | |
C6 | −0.1532 (6) | 0.42654 (14) | 0.5678 (2) | 0.0653 (8) | |
H6 | −0.2055 | 0.3962 | 0.5995 | 0.078* | |
C7 | 0.1944 (5) | 0.37188 (12) | 0.52465 (19) | 0.0554 (7) | |
C8 | 0.3820 (6) | 0.36115 (13) | 0.4756 (2) | 0.0643 (8) | |
H8 | 0.4406 | 0.3853 | 0.4336 | 0.077* | |
C9 | 0.2832 (5) | 0.28972 (13) | 0.57623 (19) | 0.0559 (7) | |
C10 | 0.0630 (5) | 0.22505 (13) | 0.6747 (2) | 0.0606 (8) | |
H10 | −0.0735 | 0.2297 | 0.6360 | 0.073* | |
C11 | 0.1131 (6) | 0.16282 (13) | 0.6878 (2) | 0.0664 (9) | |
H11A | 0.1453 | 0.1544 | 0.7493 | 0.080* | |
H11B | −0.0168 | 0.1404 | 0.6673 | 0.080* | |
C12 | 0.3231 (5) | 0.15310 (13) | 0.6329 (2) | 0.0569 (7) | |
C13 | 0.4368 (5) | 0.09940 (13) | 0.61754 (19) | 0.0566 (7) | |
C14 | 0.6347 (5) | 0.09546 (14) | 0.5673 (2) | 0.0640 (8) | |
H14 | 0.6926 | 0.1270 | 0.5402 | 0.077* | |
C15 | 0.7465 (6) | 0.04580 (14) | 0.5568 (2) | 0.0671 (9) | |
H15 | 0.8800 | 0.0445 | 0.5232 | 0.081* | |
C16 | 0.6653 (5) | −0.00304 (13) | 0.5954 (2) | 0.0618 (8) | |
C17 | 0.4650 (6) | 0.00095 (14) | 0.6425 (2) | 0.0659 (8) | |
H17 | 0.4040 | −0.0309 | 0.6677 | 0.079* | |
C18 | 0.3500 (6) | 0.05102 (14) | 0.6539 (2) | 0.0652 (8) | |
H18 | 0.2140 | 0.0521 | 0.6861 | 0.078* | |
C19 | 0.7985 (6) | −0.05603 (14) | 0.5865 (3) | 0.0827 (11) | |
H19A | 0.7180 | −0.0853 | 0.6161 | 0.124* | |
H19B | 0.9506 | −0.0516 | 0.6125 | 0.124* | |
H19C | 0.8123 | −0.0651 | 0.5253 | 0.124* | |
C20 | 0.0305 (5) | 0.25749 (12) | 0.7580 (2) | 0.0542 (7) | |
C21 | 0.1996 (5) | 0.25682 (13) | 0.8234 (2) | 0.0637 (8) | |
H21 | 0.3345 | 0.2365 | 0.8146 | 0.076* | |
C22 | 0.1749 (7) | 0.28550 (14) | 0.9016 (2) | 0.0733 (9) | |
H22 | 0.2902 | 0.2844 | 0.9452 | 0.088* | |
C23 | −0.0195 (7) | 0.31483 (13) | 0.9126 (2) | 0.0731 (10) | |
C24 | −0.1901 (7) | 0.31738 (15) | 0.8503 (3) | 0.0816 (11) | |
H24 | −0.3236 | 0.3380 | 0.8603 | 0.098* | |
C25 | −0.1649 (6) | 0.28920 (14) | 0.7719 (3) | 0.0709 (9) | |
H25 | −0.2800 | 0.2916 | 0.7284 | 0.085* | |
C26 | 1.0106 (5) | 0.09110 (13) | 0.34701 (18) | 0.0561 (7) | |
C27 | 1.2113 (6) | 0.06737 (16) | 0.3842 (2) | 0.0696 (9) | |
H27 | 1.3308 | 0.0901 | 0.4048 | 0.084* | |
C28 | 1.2335 (6) | 0.01085 (17) | 0.3907 (2) | 0.0775 (10) | |
H28 | 1.3676 | −0.0043 | 0.4157 | 0.093* | |
C29 | 1.0595 (6) | −0.02337 (15) | 0.3605 (2) | 0.0737 (10) | |
H29 | 1.0758 | −0.0617 | 0.3645 | 0.088* | |
C30 | 0.8601 (6) | −0.00060 (15) | 0.3242 (2) | 0.0731 (9) | |
H30 | 0.7405 | −0.0236 | 0.3045 | 0.088* | |
C31 | 0.8373 (6) | 0.05605 (13) | 0.3171 (2) | 0.0643 (8) | |
H31 | 0.7029 | 0.0709 | 0.2917 | 0.077* | |
C32 | 0.9822 (5) | 0.15215 (13) | 0.34277 (19) | 0.0551 (7) | |
C33 | 1.0981 (6) | 0.18976 (14) | 0.3925 (2) | 0.0644 (8) | |
H33 | 1.2110 | 0.1808 | 0.4347 | 0.077* | |
C34 | 0.8228 (5) | 0.22829 (13) | 0.2909 (2) | 0.0550 (7) | |
C35 | 0.4651 (5) | 0.24534 (12) | 0.1964 (2) | 0.0559 (8) | |
H35 | 0.3740 | 0.2246 | 0.2392 | 0.067* | |
C36 | 0.3531 (5) | 0.30230 (12) | 0.1797 (2) | 0.0619 (8) | |
H36A | 0.3483 | 0.3109 | 0.1173 | 0.074* | |
H36B | 0.1964 | 0.3034 | 0.2021 | 0.074* | |
C37 | 0.5083 (5) | 0.34182 (12) | 0.22889 (19) | 0.0544 (7) | |
C38 | 0.4623 (5) | 0.40098 (12) | 0.23963 (19) | 0.0531 (7) | |
C39 | 0.6205 (5) | 0.43590 (13) | 0.2823 (2) | 0.0608 (8) | |
H39 | 0.7594 | 0.4216 | 0.3046 | 0.073* | |
C40 | 0.5724 (6) | 0.49193 (13) | 0.2918 (2) | 0.0673 (9) | |
H40 | 0.6797 | 0.5146 | 0.3207 | 0.081* | |
C41 | 0.3681 (6) | 0.51480 (13) | 0.2591 (2) | 0.0619 (8) | |
C42 | 0.2136 (6) | 0.48056 (13) | 0.2167 (2) | 0.0646 (8) | |
H42 | 0.0760 | 0.4952 | 0.1938 | 0.077* | |
C43 | 0.2585 (5) | 0.42450 (12) | 0.2075 (2) | 0.0629 (8) | |
H43 | 0.1493 | 0.4021 | 0.1790 | 0.075* | |
C44 | 0.3189 (8) | 0.57637 (13) | 0.2676 (3) | 0.0901 (12) | |
H44A | 0.3506 | 0.5880 | 0.3270 | 0.135* | |
H44B | 0.1588 | 0.5834 | 0.2529 | 0.135* | |
H44C | 0.4163 | 0.5966 | 0.2281 | 0.135* | |
C45 | 0.4915 (5) | 0.21170 (11) | 0.1141 (2) | 0.0520 (7) | |
C46 | 0.6698 (5) | 0.21963 (12) | 0.0566 (2) | 0.0607 (8) | |
H46 | 0.7872 | 0.2447 | 0.0711 | 0.073* | |
C47 | 0.6789 (6) | 0.19115 (13) | −0.0227 (2) | 0.0671 (8) | |
H47 | 0.8014 | 0.1963 | −0.0610 | 0.081* | |
C48 | 0.5029 (7) | 0.15541 (13) | −0.0426 (2) | 0.0689 (9) | |
C49 | 0.3243 (7) | 0.14560 (14) | 0.0122 (3) | 0.0758 (10) | |
H49 | 0.2083 | 0.1204 | −0.0031 | 0.091* | |
C50 | 0.3179 (6) | 0.17378 (13) | 0.0911 (3) | 0.0696 (9) | |
H50 | 0.1964 | 0.1674 | 0.1294 | 0.084* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0668 (5) | 0.0716 (5) | 0.0607 (5) | −0.0069 (4) | 0.0122 (4) | −0.0014 (4) |
S2 | 0.0692 (5) | 0.0773 (5) | 0.0529 (5) | 0.0069 (4) | −0.0124 (4) | −0.0081 (4) |
F1 | 0.177 (2) | 0.0779 (13) | 0.0908 (16) | −0.0016 (15) | 0.0292 (17) | −0.0204 (13) |
F2 | 0.1388 (19) | 0.0879 (13) | 0.0854 (15) | −0.0013 (14) | −0.0106 (15) | −0.0298 (13) |
N1 | 0.0642 (15) | 0.0663 (15) | 0.0432 (14) | −0.0055 (13) | 0.0048 (12) | 0.0038 (12) |
N2 | 0.0670 (16) | 0.0699 (16) | 0.0547 (16) | 0.0006 (13) | 0.0104 (13) | 0.0083 (13) |
N3 | 0.0647 (16) | 0.0700 (17) | 0.0518 (16) | 0.0040 (13) | 0.0053 (13) | 0.0062 (13) |
N4 | 0.0555 (14) | 0.0685 (16) | 0.0512 (15) | 0.0116 (12) | −0.0105 (12) | 0.0020 (13) |
N5 | 0.0650 (15) | 0.0591 (15) | 0.0655 (17) | 0.0098 (12) | −0.0209 (13) | −0.0019 (13) |
N6 | 0.0581 (14) | 0.0603 (14) | 0.0582 (16) | 0.0021 (12) | −0.0104 (13) | −0.0035 (12) |
C1 | 0.0609 (18) | 0.0634 (18) | 0.0467 (17) | −0.0098 (15) | −0.0093 (14) | −0.0040 (14) |
C2 | 0.072 (2) | 0.083 (2) | 0.067 (2) | −0.0057 (19) | 0.0038 (18) | 0.0146 (18) |
C3 | 0.086 (3) | 0.077 (2) | 0.084 (3) | 0.007 (2) | 0.001 (2) | 0.021 (2) |
C4 | 0.095 (3) | 0.075 (2) | 0.080 (3) | 0.012 (2) | −0.013 (2) | 0.003 (2) |
C5 | 0.065 (2) | 0.097 (3) | 0.065 (2) | −0.001 (2) | 0.0001 (17) | −0.010 (2) |
C6 | 0.067 (2) | 0.074 (2) | 0.0554 (19) | −0.0061 (17) | 0.0055 (16) | −0.0052 (16) |
C7 | 0.0610 (18) | 0.0633 (18) | 0.0418 (16) | −0.0145 (15) | −0.0016 (14) | −0.0017 (14) |
C8 | 0.071 (2) | 0.0666 (18) | 0.0557 (19) | −0.0123 (16) | 0.0138 (17) | 0.0013 (16) |
C9 | 0.0605 (17) | 0.0673 (18) | 0.0400 (16) | −0.0059 (15) | −0.0001 (14) | 0.0010 (14) |
C10 | 0.0497 (16) | 0.077 (2) | 0.0553 (19) | −0.0016 (15) | −0.0042 (15) | 0.0081 (16) |
C11 | 0.066 (2) | 0.070 (2) | 0.063 (2) | −0.0097 (16) | 0.0016 (17) | 0.0006 (16) |
C12 | 0.0578 (17) | 0.0697 (19) | 0.0431 (16) | −0.0068 (15) | −0.0077 (14) | 0.0023 (15) |
C13 | 0.0549 (17) | 0.0694 (19) | 0.0454 (17) | −0.0034 (15) | −0.0060 (14) | −0.0019 (15) |
C14 | 0.067 (2) | 0.070 (2) | 0.0549 (19) | −0.0090 (16) | −0.0011 (16) | 0.0005 (15) |
C15 | 0.0645 (19) | 0.083 (2) | 0.0536 (19) | −0.0008 (18) | 0.0027 (16) | −0.0129 (18) |
C16 | 0.066 (2) | 0.070 (2) | 0.0495 (18) | −0.0079 (16) | −0.0076 (16) | −0.0106 (16) |
C17 | 0.072 (2) | 0.0660 (19) | 0.060 (2) | −0.0098 (17) | −0.0073 (17) | 0.0031 (16) |
C18 | 0.0619 (18) | 0.078 (2) | 0.055 (2) | −0.0063 (17) | 0.0025 (15) | 0.0022 (17) |
C19 | 0.093 (3) | 0.076 (2) | 0.079 (3) | 0.002 (2) | −0.003 (2) | −0.018 (2) |
C20 | 0.0501 (16) | 0.0601 (16) | 0.0524 (18) | −0.0029 (14) | 0.0026 (14) | 0.0095 (14) |
C21 | 0.0591 (18) | 0.0691 (19) | 0.063 (2) | 0.0061 (15) | −0.0053 (16) | 0.0031 (16) |
C22 | 0.086 (2) | 0.074 (2) | 0.061 (2) | −0.0015 (19) | −0.0048 (19) | −0.0029 (18) |
C23 | 0.101 (3) | 0.0535 (18) | 0.065 (2) | −0.0041 (19) | 0.018 (2) | −0.0044 (17) |
C24 | 0.079 (2) | 0.072 (2) | 0.094 (3) | 0.0243 (19) | 0.025 (2) | 0.012 (2) |
C25 | 0.064 (2) | 0.076 (2) | 0.072 (2) | 0.0103 (17) | 0.0082 (18) | 0.0179 (19) |
C26 | 0.0527 (17) | 0.0735 (19) | 0.0421 (16) | 0.0104 (15) | −0.0006 (13) | 0.0056 (14) |
C27 | 0.0572 (18) | 0.086 (2) | 0.065 (2) | 0.0125 (16) | −0.0054 (16) | 0.0035 (17) |
C28 | 0.072 (2) | 0.090 (3) | 0.070 (2) | 0.032 (2) | −0.0053 (18) | 0.011 (2) |
C29 | 0.089 (2) | 0.075 (2) | 0.057 (2) | 0.021 (2) | −0.0019 (19) | 0.0079 (18) |
C30 | 0.082 (2) | 0.074 (2) | 0.063 (2) | 0.0094 (18) | −0.0098 (18) | 0.0033 (17) |
C31 | 0.0614 (18) | 0.075 (2) | 0.056 (2) | 0.0131 (17) | −0.0110 (15) | 0.0077 (16) |
C32 | 0.0491 (16) | 0.0733 (19) | 0.0427 (16) | 0.0079 (14) | −0.0031 (13) | 0.0041 (15) |
C33 | 0.0628 (18) | 0.084 (2) | 0.0461 (18) | 0.0082 (16) | −0.0112 (15) | 0.0038 (16) |
C34 | 0.0531 (16) | 0.0656 (18) | 0.0464 (17) | 0.0087 (15) | −0.0025 (13) | −0.0003 (15) |
C35 | 0.0519 (16) | 0.0605 (17) | 0.0549 (18) | −0.0004 (13) | −0.0085 (14) | 0.0037 (14) |
C36 | 0.0619 (18) | 0.0592 (18) | 0.064 (2) | 0.0058 (15) | −0.0104 (16) | 0.0040 (15) |
C37 | 0.0552 (17) | 0.0613 (17) | 0.0465 (17) | 0.0025 (14) | −0.0024 (14) | 0.0037 (14) |
C38 | 0.0543 (16) | 0.0603 (17) | 0.0447 (16) | −0.0033 (14) | 0.0028 (13) | 0.0045 (14) |
C39 | 0.0578 (18) | 0.0704 (19) | 0.0540 (18) | −0.0023 (15) | −0.0047 (15) | 0.0073 (16) |
C40 | 0.074 (2) | 0.067 (2) | 0.061 (2) | −0.0159 (17) | −0.0003 (18) | −0.0023 (17) |
C41 | 0.073 (2) | 0.0603 (18) | 0.0528 (18) | −0.0029 (16) | 0.0070 (16) | 0.0015 (15) |
C42 | 0.0629 (19) | 0.0662 (19) | 0.065 (2) | 0.0081 (16) | −0.0029 (16) | 0.0008 (17) |
C43 | 0.0617 (18) | 0.0603 (18) | 0.066 (2) | 0.0000 (15) | −0.0092 (16) | −0.0009 (16) |
C44 | 0.116 (3) | 0.062 (2) | 0.092 (3) | 0.003 (2) | −0.004 (2) | −0.004 (2) |
C45 | 0.0508 (16) | 0.0504 (15) | 0.0544 (18) | −0.0006 (13) | −0.0078 (15) | 0.0096 (13) |
C46 | 0.0610 (18) | 0.0540 (16) | 0.067 (2) | −0.0112 (14) | −0.0064 (17) | 0.0056 (16) |
C47 | 0.072 (2) | 0.0654 (18) | 0.064 (2) | −0.0014 (17) | 0.0083 (17) | 0.0076 (17) |
C48 | 0.086 (2) | 0.0556 (18) | 0.065 (2) | 0.0055 (17) | −0.012 (2) | −0.0073 (16) |
C49 | 0.078 (2) | 0.068 (2) | 0.081 (3) | −0.0147 (18) | −0.013 (2) | −0.0119 (19) |
C50 | 0.0591 (18) | 0.0695 (19) | 0.080 (2) | −0.0128 (16) | −0.0003 (17) | 0.0046 (19) |
S1—C8 | 1.719 (3) | C20—C25 | 1.379 (4) |
S1—C9 | 1.724 (3) | C21—C22 | 1.384 (5) |
S2—C33 | 1.719 (3) | C21—H21 | 0.9300 |
S2—C34 | 1.723 (3) | C22—C23 | 1.337 (5) |
F1—C23 | 1.371 (4) | C22—H22 | 0.9300 |
F2—C48 | 1.369 (4) | C23—C24 | 1.353 (5) |
N1—C9 | 1.297 (4) | C24—C25 | 1.381 (5) |
N1—C7 | 1.393 (4) | C24—H24 | 0.9300 |
N2—C9 | 1.386 (4) | C25—H25 | 0.9300 |
N2—N3 | 1.393 (4) | C26—C31 | 1.379 (4) |
N2—C10 | 1.479 (4) | C26—C27 | 1.400 (4) |
N3—C12 | 1.288 (4) | C26—C32 | 1.483 (4) |
N4—C34 | 1.294 (4) | C27—C28 | 1.373 (5) |
N4—C32 | 1.396 (3) | C27—H27 | 0.9300 |
N5—C34 | 1.384 (3) | C28—C29 | 1.370 (5) |
N5—N6 | 1.396 (3) | C28—H28 | 0.9300 |
N5—C35 | 1.489 (3) | C29—C30 | 1.379 (5) |
N6—C37 | 1.286 (3) | C29—H29 | 0.9300 |
C1—C6 | 1.381 (4) | C30—C31 | 1.377 (5) |
C1—C2 | 1.399 (4) | C30—H30 | 0.9300 |
C1—C7 | 1.476 (4) | C31—H31 | 0.9300 |
C2—C3 | 1.379 (5) | C32—C33 | 1.349 (4) |
C2—H2A | 0.9300 | C33—H33 | 0.9300 |
C3—C4 | 1.364 (5) | C35—C45 | 1.500 (4) |
C3—H3 | 0.9300 | C35—C36 | 1.537 (4) |
C4—C5 | 1.377 (5) | C35—H35 | 0.9800 |
C4—H4 | 0.9300 | C36—C37 | 1.498 (4) |
C5—C6 | 1.384 (5) | C36—H36A | 0.9700 |
C5—H5 | 0.9300 | C36—H36B | 0.9700 |
C6—H6 | 0.9300 | C37—C38 | 1.461 (4) |
C7—C8 | 1.347 (4) | C38—C43 | 1.385 (4) |
C8—H8 | 0.9300 | C38—C39 | 1.392 (4) |
C10—C20 | 1.502 (4) | C39—C40 | 1.388 (4) |
C10—C11 | 1.541 (4) | C39—H39 | 0.9300 |
C10—H10 | 0.9800 | C40—C41 | 1.384 (4) |
C11—C12 | 1.498 (5) | C40—H40 | 0.9300 |
C11—H11A | 0.9700 | C41—C42 | 1.366 (4) |
C11—H11B | 0.9700 | C41—C44 | 1.518 (4) |
C12—C13 | 1.472 (4) | C42—C43 | 1.384 (4) |
C13—C14 | 1.384 (4) | C42—H42 | 0.9300 |
C13—C18 | 1.388 (4) | C43—H43 | 0.9300 |
C14—C15 | 1.371 (4) | C44—H44A | 0.9600 |
C14—H14 | 0.9300 | C44—H44B | 0.9600 |
C15—C16 | 1.400 (5) | C44—H44C | 0.9600 |
C15—H15 | 0.9300 | C45—C46 | 1.372 (4) |
C16—C17 | 1.370 (4) | C45—C50 | 1.395 (4) |
C16—C19 | 1.498 (5) | C46—C47 | 1.388 (5) |
C17—C18 | 1.390 (5) | C46—H46 | 0.9300 |
C17—H17 | 0.9300 | C47—C48 | 1.360 (5) |
C18—H18 | 0.9300 | C47—H47 | 0.9300 |
C19—H19A | 0.9600 | C48—C49 | 1.354 (5) |
C19—H19B | 0.9600 | C49—C50 | 1.378 (5) |
C19—H19C | 0.9600 | C49—H49 | 0.9300 |
C20—C21 | 1.379 (4) | C50—H50 | 0.9300 |
C8—S1—C9 | 87.38 (16) | C23—C24—C25 | 119.7 (3) |
C33—S2—C34 | 87.58 (14) | C23—C24—H24 | 120.2 |
C9—N1—C7 | 108.8 (3) | C25—C24—H24 | 120.2 |
C9—N2—N3 | 116.0 (3) | C20—C25—C24 | 120.2 (3) |
C9—N2—C10 | 123.0 (2) | C20—C25—H25 | 119.9 |
N3—N2—C10 | 113.1 (2) | C24—C25—H25 | 119.9 |
C12—N3—N2 | 108.2 (3) | C31—C26—C27 | 118.0 (3) |
C34—N4—C32 | 109.2 (2) | C31—C26—C32 | 121.1 (2) |
C34—N5—N6 | 115.1 (2) | C27—C26—C32 | 120.9 (3) |
C34—N5—C35 | 123.0 (2) | C28—C27—C26 | 120.7 (3) |
N6—N5—C35 | 112.4 (2) | C28—C27—H27 | 119.7 |
C37—N6—N5 | 108.6 (2) | C26—C27—H27 | 119.7 |
C6—C1—C2 | 117.9 (3) | C29—C28—C27 | 120.5 (3) |
C6—C1—C7 | 121.5 (3) | C29—C28—H28 | 119.7 |
C2—C1—C7 | 120.6 (3) | C27—C28—H28 | 119.7 |
C3—C2—C1 | 120.7 (4) | C28—C29—C30 | 119.5 (3) |
C3—C2—H2A | 119.6 | C28—C29—H29 | 120.2 |
C1—C2—H2A | 119.6 | C30—C29—H29 | 120.2 |
C4—C3—C2 | 120.7 (4) | C31—C30—C29 | 120.3 (3) |
C4—C3—H3 | 119.6 | C31—C30—H30 | 119.9 |
C2—C3—H3 | 119.6 | C29—C30—H30 | 119.9 |
C3—C4—C5 | 119.4 (4) | C30—C31—C26 | 121.0 (3) |
C3—C4—H4 | 120.3 | C30—C31—H31 | 119.5 |
C5—C4—H4 | 120.3 | C26—C31—H31 | 119.5 |
C4—C5—C6 | 120.5 (4) | C33—C32—N4 | 114.5 (3) |
C4—C5—H5 | 119.7 | C33—C32—C26 | 126.2 (2) |
C6—C5—H5 | 119.7 | N4—C32—C26 | 119.3 (3) |
C5—C6—C1 | 120.8 (3) | C32—C33—S2 | 111.6 (2) |
C5—C6—H6 | 119.6 | C32—C33—H33 | 124.2 |
C1—C6—H6 | 119.6 | S2—C33—H33 | 124.2 |
C8—C7—N1 | 114.9 (3) | N4—C34—N5 | 122.8 (3) |
C8—C7—C1 | 126.6 (3) | N4—C34—S2 | 117.1 (2) |
N1—C7—C1 | 118.5 (3) | N5—C34—S2 | 120.0 (2) |
C7—C8—S1 | 111.6 (2) | N5—C35—C45 | 113.6 (3) |
C7—C8—H8 | 124.2 | N5—C35—C36 | 100.2 (2) |
S1—C8—H8 | 124.2 | C45—C35—C36 | 113.2 (2) |
N1—C9—N2 | 122.6 (3) | N5—C35—H35 | 109.8 |
N1—C9—S1 | 117.3 (2) | C45—C35—H35 | 109.8 |
N2—C9—S1 | 120.1 (2) | C36—C35—H35 | 109.8 |
N2—C10—C20 | 111.9 (2) | C37—C36—C35 | 104.0 (2) |
N2—C10—C11 | 100.6 (2) | C37—C36—H36A | 111.0 |
C20—C10—C11 | 115.1 (3) | C35—C36—H36A | 111.0 |
N2—C10—H10 | 109.6 | C37—C36—H36B | 111.0 |
C20—C10—H10 | 109.6 | C35—C36—H36B | 111.0 |
C11—C10—H10 | 109.6 | H36A—C36—H36B | 109.0 |
C12—C11—C10 | 103.4 (3) | N6—C37—C38 | 122.2 (3) |
C12—C11—H11A | 111.1 | N6—C37—C36 | 113.1 (3) |
C10—C11—H11A | 111.1 | C38—C37—C36 | 124.7 (2) |
C12—C11—H11B | 111.1 | C43—C38—C39 | 117.4 (3) |
C10—C11—H11B | 111.1 | C43—C38—C37 | 121.0 (3) |
H11A—C11—H11B | 109.0 | C39—C38—C37 | 121.6 (3) |
N3—C12—C13 | 120.1 (3) | C40—C39—C38 | 120.5 (3) |
N3—C12—C11 | 113.6 (3) | C40—C39—H39 | 119.7 |
C13—C12—C11 | 126.2 (3) | C38—C39—H39 | 119.7 |
C14—C13—C18 | 117.8 (3) | C41—C40—C39 | 121.4 (3) |
C14—C13—C12 | 121.3 (3) | C41—C40—H40 | 119.3 |
C18—C13—C12 | 120.8 (3) | C39—C40—H40 | 119.3 |
C15—C14—C13 | 121.1 (3) | C42—C41—C40 | 118.1 (3) |
C15—C14—H14 | 119.5 | C42—C41—C44 | 120.7 (3) |
C13—C14—H14 | 119.5 | C40—C41—C44 | 121.2 (3) |
C14—C15—C16 | 121.8 (3) | C41—C42—C43 | 121.1 (3) |
C14—C15—H15 | 119.1 | C41—C42—H42 | 119.4 |
C16—C15—H15 | 119.1 | C43—C42—H42 | 119.4 |
C17—C16—C15 | 116.7 (3) | C38—C43—C42 | 121.5 (3) |
C17—C16—C19 | 122.9 (3) | C38—C43—H43 | 119.2 |
C15—C16—C19 | 120.4 (3) | C42—C43—H43 | 119.2 |
C16—C17—C18 | 122.2 (3) | C41—C44—H44A | 109.5 |
C16—C17—H17 | 118.9 | C41—C44—H44B | 109.5 |
C18—C17—H17 | 118.9 | H44A—C44—H44B | 109.5 |
C17—C18—C13 | 120.4 (3) | C41—C44—H44C | 109.5 |
C17—C18—H18 | 119.8 | H44A—C44—H44C | 109.5 |
C13—C18—H18 | 119.8 | H44B—C44—H44C | 109.5 |
C16—C19—H19A | 109.5 | C46—C45—C50 | 118.2 (3) |
C16—C19—H19B | 109.5 | C46—C45—C35 | 122.8 (3) |
H19A—C19—H19B | 109.5 | C50—C45—C35 | 118.8 (3) |
C16—C19—H19C | 109.5 | C45—C46—C47 | 121.5 (3) |
H19A—C19—H19C | 109.5 | C45—C46—H46 | 119.3 |
H19B—C19—H19C | 109.5 | C47—C46—H46 | 119.3 |
C21—C20—C25 | 117.7 (3) | C48—C47—C46 | 117.9 (3) |
C21—C20—C10 | 120.2 (3) | C48—C47—H47 | 121.1 |
C25—C20—C10 | 122.1 (3) | C46—C47—H47 | 121.1 |
C20—C21—C22 | 122.0 (3) | C49—C48—C47 | 123.0 (3) |
C20—C21—H21 | 119.0 | C49—C48—F2 | 118.7 (3) |
C22—C21—H21 | 119.0 | C47—C48—F2 | 118.3 (4) |
C23—C22—C21 | 118.0 (3) | C48—C49—C50 | 118.6 (3) |
C23—C22—H22 | 121.0 | C48—C49—H49 | 120.7 |
C21—C22—H22 | 121.0 | C50—C49—H49 | 120.7 |
C22—C23—C24 | 122.4 (3) | C49—C50—C45 | 120.8 (4) |
C22—C23—F1 | 119.0 (4) | C49—C50—H50 | 119.6 |
C24—C23—F1 | 118.6 (4) | C45—C50—H50 | 119.6 |
C9—N2—N3—C12 | −157.5 (2) | C10—C20—C25—C24 | 178.5 (3) |
C10—N2—N3—C12 | −7.5 (3) | C23—C24—C25—C20 | 1.6 (5) |
C34—N5—N6—C37 | −157.5 (3) | C31—C26—C27—C28 | −0.2 (5) |
C35—N5—N6—C37 | −10.0 (3) | C32—C26—C27—C28 | 177.8 (3) |
C6—C1—C2—C3 | 0.8 (5) | C26—C27—C28—C29 | 0.2 (5) |
C7—C1—C2—C3 | −177.7 (3) | C27—C28—C29—C30 | −0.6 (6) |
C1—C2—C3—C4 | −2.0 (5) | C28—C29—C30—C31 | 1.0 (5) |
C2—C3—C4—C5 | 1.8 (6) | C29—C30—C31—C26 | −1.0 (5) |
C3—C4—C5—C6 | −0.5 (5) | C27—C26—C31—C30 | 0.5 (5) |
C4—C5—C6—C1 | −0.7 (5) | C32—C26—C31—C30 | −177.4 (3) |
C2—C1—C6—C5 | 0.5 (4) | C34—N4—C32—C33 | 1.2 (4) |
C7—C1—C6—C5 | 179.0 (3) | C34—N4—C32—C26 | −180.0 (3) |
C9—N1—C7—C8 | 0.6 (3) | C31—C26—C32—C33 | 157.8 (3) |
C9—N1—C7—C1 | −178.6 (2) | C27—C26—C32—C33 | −20.1 (5) |
C6—C1—C7—C8 | 171.7 (3) | C31—C26—C32—N4 | −20.9 (4) |
C2—C1—C7—C8 | −9.8 (4) | C27—C26—C32—N4 | 161.2 (3) |
C6—C1—C7—N1 | −9.2 (4) | N4—C32—C33—S2 | −0.4 (4) |
C2—C1—C7—N1 | 169.3 (3) | C26—C32—C33—S2 | −179.1 (3) |
N1—C7—C8—S1 | −0.3 (3) | C34—S2—C33—C32 | −0.3 (3) |
C1—C7—C8—S1 | 178.8 (2) | C32—N4—C34—N5 | 175.9 (3) |
C9—S1—C8—C7 | 0.0 (2) | C32—N4—C34—S2 | −1.5 (4) |
C7—N1—C9—N2 | 178.3 (2) | N6—N5—C34—N4 | 171.7 (3) |
C7—N1—C9—S1 | −0.7 (3) | C35—N5—C34—N4 | 28.0 (5) |
N3—N2—C9—N1 | 166.1 (3) | N6—N5—C34—S2 | −10.9 (4) |
C10—N2—C9—N1 | 19.3 (4) | C35—N5—C34—S2 | −154.7 (2) |
N3—N2—C9—S1 | −15.0 (3) | C33—S2—C34—N4 | 1.1 (3) |
C10—N2—C9—S1 | −161.7 (2) | C33—S2—C34—N5 | −176.4 (3) |
C8—S1—C9—N1 | 0.4 (2) | C34—N5—C35—C45 | −81.5 (4) |
C8—S1—C9—N2 | −178.6 (2) | N6—N5—C35—C45 | 133.9 (3) |
C9—N2—C10—C20 | −78.9 (3) | C34—N5—C35—C36 | 157.5 (3) |
N3—N2—C10—C20 | 133.5 (2) | N6—N5—C35—C36 | 12.9 (3) |
C9—N2—C10—C11 | 158.3 (3) | N5—C35—C36—C37 | −10.7 (3) |
N3—N2—C10—C11 | 10.7 (3) | C45—C35—C36—C37 | −132.0 (3) |
N2—C10—C11—C12 | −9.4 (3) | N5—N6—C37—C38 | −177.7 (3) |
C20—C10—C11—C12 | −129.9 (3) | N5—N6—C37—C36 | 1.9 (4) |
N2—N3—C12—C13 | −177.4 (2) | C35—C36—C37—N6 | 6.2 (4) |
N2—N3—C12—C11 | 0.4 (3) | C35—C36—C37—C38 | −174.2 (3) |
C10—C11—C12—N3 | 6.2 (3) | N6—C37—C38—C43 | −177.0 (3) |
C10—C11—C12—C13 | −176.1 (3) | C36—C37—C38—C43 | 3.4 (5) |
N3—C12—C13—C14 | −0.7 (4) | N6—C37—C38—C39 | 3.1 (5) |
C11—C12—C13—C14 | −178.2 (3) | C36—C37—C38—C39 | −176.5 (3) |
N3—C12—C13—C18 | 178.6 (3) | C43—C38—C39—C40 | 0.2 (5) |
C11—C12—C13—C18 | 1.1 (4) | C37—C38—C39—C40 | −179.9 (3) |
C18—C13—C14—C15 | −2.6 (4) | C38—C39—C40—C41 | −0.3 (5) |
C12—C13—C14—C15 | 176.7 (3) | C39—C40—C41—C42 | −0.1 (5) |
C13—C14—C15—C16 | 0.6 (4) | C39—C40—C41—C44 | −178.4 (3) |
C14—C15—C16—C17 | 1.5 (4) | C40—C41—C42—C43 | 0.6 (5) |
C14—C15—C16—C19 | −176.8 (3) | C44—C41—C42—C43 | 179.0 (3) |
C15—C16—C17—C18 | −1.7 (4) | C39—C38—C43—C42 | 0.4 (5) |
C19—C16—C17—C18 | 176.6 (3) | C37—C38—C43—C42 | −179.6 (3) |
C16—C17—C18—C13 | −0.3 (4) | C41—C42—C43—C38 | −0.8 (5) |
C14—C13—C18—C17 | 2.4 (4) | N5—C35—C45—C46 | −32.9 (4) |
C12—C13—C18—C17 | −176.9 (3) | C36—C35—C45—C46 | 80.5 (3) |
N2—C10—C20—C21 | −58.9 (4) | N5—C35—C45—C50 | 152.4 (3) |
C11—C10—C20—C21 | 55.1 (4) | C36—C35—C45—C50 | −94.2 (3) |
N2—C10—C20—C25 | 120.4 (3) | C50—C45—C46—C47 | 0.3 (4) |
C11—C10—C20—C25 | −125.6 (3) | C35—C45—C46—C47 | −174.5 (3) |
C25—C20—C21—C22 | 1.7 (5) | C45—C46—C47—C48 | 0.9 (5) |
C10—C20—C21—C22 | −179.1 (3) | C46—C47—C48—C49 | −1.7 (5) |
C20—C21—C22—C23 | −0.5 (5) | C46—C47—C48—F2 | 179.4 (3) |
C21—C22—C23—C24 | −0.2 (6) | C47—C48—C49—C50 | 1.2 (5) |
C21—C22—C23—F1 | 178.0 (3) | F2—C48—C49—C50 | −179.9 (3) |
C22—C23—C24—C25 | −0.4 (6) | C48—C49—C50—C45 | 0.1 (5) |
F1—C23—C24—C25 | −178.6 (3) | C46—C45—C50—C49 | −0.8 (4) |
C21—C20—C25—C24 | −2.2 (5) | C35—C45—C50—C49 | 174.2 (3) |
Cg1, Cg2, Cg3 and Cg4 are the centroids of the C26–C31, C45–C50, S2,N4,C32–C34 and C1–C6 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···Cg1 | 0.93 | 2.75 | 3.537 (3) | 143 |
C19—H19A···Cg2i | 0.96 | 2.94 | 3.596 (4) | 127 |
C35—H35···Cg3ii | 0.98 | 2.94 | 3.843 (3) | 153 |
C42—H42···Cg4iii | 0.93 | 2.86 | 3.567 (3) | 134 |
Symmetry codes: (i) x, −y, z+1/2; (ii) x−1, y, z; (iii) x, −y+1, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C25H20FN3S |
Mr | 413.50 |
Crystal system, space group | Monoclinic, Pc |
Temperature (K) | 295 |
a, b, c (Å) | 5.7563 (3), 24.1214 (12), 15.1827 (8) |
β (°) | 90.948 (5) |
V (Å3) | 2107.83 (19) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.18 |
Crystal size (mm) | 0.40 × 0.30 × 0.20 |
Data collection | |
Diffractometer | Agilent SuperNova Dual diffractometer with an Atlas detector |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2011) |
Tmin, Tmax | 0.837, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 22651, 9054, 5841 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.651 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.117, 0.99 |
No. of reflections | 9054 |
No. of parameters | 543 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.16 |
Absolute structure | Flack (1983), 4165 Friedel pairs |
Absolute structure parameter | −0.06 (6) |
Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).
Cg1, Cg2, Cg3 and Cg4 are the centroids of the C26–C31, C45–C50, S2,N4,C32–C34 and C1–C6 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···Cg1 | 0.93 | 2.75 | 3.537 (3) | 143 |
C19—H19A···Cg2i | 0.96 | 2.94 | 3.596 (4) | 127 |
C35—H35···Cg3ii | 0.98 | 2.94 | 3.843 (3) | 153 |
C42—H42···Cg4iii | 0.93 | 2.86 | 3.567 (3) | 134 |
Symmetry codes: (i) x, −y, z+1/2; (ii) x−1, y, z; (iii) x, −y+1, z−1/2. |
Footnotes
‡Additional correspondence author, e-mail: bakrfatehy@yahoo.com.
Acknowledgements
We thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The title compound (I) was investigated in relation to the established biological activities exhibited by pyrazolin-1-ylthiazoles (Abdel-Wahab et al., 2012; Abdel-Wahab et al., 2009; Chimenti et al., 2010).
Two independent molecules comprise the crystallographic asymmetric unit of (I), Fig. 1. As judged from the overlay diagram, Fig. 2, the central residues are super-imposable with the major difference relating to the relative orientations of the fluorobenzene rings with the dihedral angle formed with the least-squares plane through the pyrazolyl ring being 89.39 (17)° for the S1-containing molecule and 75.23 (16)° for the second molecule. Each pyrazolyl ring adopts an envelope conformation with the methine-C atom, i.e. C10 and C35, being the flap atom in each case. With the exception of the near perpendicular relationship between the pyrazolyl and fluorobenzene rings, the remaining components of the molecule exhibit relatively small twists as indicated by the dihedral angles formed between the five-membered rings [18.23 (16); 17.84 (16)°], the thiazolyl and attached phenyl ring [10.26 (16); 20.87 (15)°], and between the pyrazolyl and appended tolyl ring [2.37 (16); 1.96 (16)°]. Overall, the molecule has the shape of the letter T and resembles the structure of a literature precedent (Fun et al., 2011).
The crystal packing is dominated by C—H···π interactions that lead to a three-dimensional architecture, Fig. 3 and Table 1.